LMsA: I think he enjoys rubbing people’s faces into it when he takes off on holidays and makes little or no attempt to conceal it.
He lacks self-awareness. He probably noticed that he gets supportive messages when he posts vacation pictures, so he doesn't miss the opportunity to upload them. In light of his claims of financial struggles, he does not recognize how bad this looks. If asked, he would probably gripe that people don't understand the strain he is under and are paying too much attention to his every move, and so on. The notion that people might justifiably draw an adverse conclusion from his actions is incomprehensible to him.
This inability to step outside of himself and see his situation the way an outsider would is one of the biggest reasons that he keeps struggling. If you don't believe that you ever make mistakes, then you cannot learn from your mistakes.